Hydrochloric Acid → Benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate

HRID 1154219Notes

Reaction equation

HRID 1154219 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:42]1[N:43]=[C:44]([NH:47]C=O)[S:45][CH:46]=1)[C:12]([NH:14][CH:15]1[C:40](=[O:41])[N:17]2[C:18]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:19]([CH:22]=[CH2:23])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(=O)(O)[O-].[Na+].C(OC(C)C)(C)C>CO.O>[NH2:47][C:44]1[S:45][CH:46]=[C:42]([C:11](=[N:10][O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:12]([NH:14][CH:15]2[C:40](=[O:41])[N:17]3[C:18]([C:24]([O:26][CH:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:25])=[C:19]([CH:22]=[CH2:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:43]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 516892Sodium BicarbonateHCID 131713176Benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 131713177Benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylateYield 83.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (19.0 g) and conc. hydrochloric acid (11.6 g) in methanol (380 ml) was stirred at ambient temperature for 15 minutes. After addition of water (200 ml), the reaction mixture was neutralized with sodium bicarbonate, followed by removing the methanol under reduced pressure. The resultant aqueous solution was extracted three times with ethyl acetate, and the combined extract was washed with water and an aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. Removal of the solvent gave an oil, which was pulverized with diisopropyl ether to obtain benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (15.3 g).

Workup

  1. customby removing the methanol under reduced pressure
  2. extractionThe resultant aqueous solution was extracted three times with ethyl acetate
  3. extractionthe combined extract
  4. washwas washed with water
  5. dry with materialan aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  6. customRemoval of the solvent
  7. customgave an oil, which

Sources & evidence

ORD record
ord-88169eab0c9240cf91ae975bae0e82a9
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

Loading…